(3S,4R,5R,6S)-8-Benzyloxy-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-octan-2-one

Base Information

Chemical Name:(3S,4R,5R,6S)-8-Benzyloxy-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-octan-2-one
CAS No.:899798-78-8
Molecular Formula:C₂₉H₅₄O₄Si₂
Molecular Weight:522.916
Hs Code.:

Synonyms:(3S,4R,5R,6S)-8-Benzyloxy-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-octan-2-one

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Chemical Property of (3S,4R,5R,6S)-8-Benzyloxy-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-octan-2-one

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Technology Process of (3S,4R,5R,6S)-8-Benzyloxy-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-octan-2-one

There total 12 articles about (3S,4R,5R,6S)-8-Benzyloxy-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-octan-2-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 78.0%

: 899798-77-7
(2S,3R,4R,5S)-7-Benzyloxy-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-heptanoic acid methoxy-methyl-amide

: 75-16-1
methylmagnesium bromide

: 899798-78-8
(3S,4R,5R,6S)-8-Benzyloxy-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-octan-2-one

Guidance literature:: In tetrahydrofuran; diethyl ether; at -20 - 0 ℃; for 1.25h;
DOI:10.1021/ol060669w

Reference yield:

: 872369-17-0
(2R,3S)-5-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-2-methylpentanal

: 899798-78-8
(3S,4R,5R,6S)-8-Benzyloxy-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-octan-2-one

Guidance literature:: Multi-step reaction with 5 steps

1: CH₂Cl₂ / 16 h / -78 °C

2: 2,6-lutidine / CH₂Cl₂ / 1 h / Heating

3: aq. LiOH; H₂O₂ / tetrahydrofuran / 24 h / 20 °C

4: 1,1'-carbonyl-diimidazole / CH₂Cl₂ / 16 h / 20 °C

5: 78 percent / tetrahydrofuran / 1 h / 0 °C

With 2,6-dimethylpyridine; lithium hydroxide; dihydrogen peroxide; 1,1'-carbonyldiimidazole; In tetrahydrofuran; dichloromethane; 1: Evans asymmetric aldolization;
DOI:10.1002/chem.200700342

Reference yield:

: 899798-76-6
(2S,3R,4R,5S)-7-Benzyloxy-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-heptanoic acid

: 899798-78-8
(3S,4R,5R,6S)-8-Benzyloxy-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-octan-2-one

Guidance literature:: Multi-step reaction with 2 steps

1: 1,1'-carbonyl-diimidazole / CH₂Cl₂ / 16 h / 20 °C

2: 78 percent / tetrahydrofuran / 1 h / 0 °C

With 1,1'-carbonyldiimidazole; In tetrahydrofuran; dichloromethane;
DOI:10.1002/chem.200700342